The most recommended retirement books

This books takes the opposite approach to The Simple Path To Wealth; it covers a vast range of financial topics and historical figures while diving deep into the mathematics of a rational retirement plan. This book can be a challenging read at times, but it will make you smarter. Consider this a graduate school-level education in retirement.

As head of the Yale University endowment fund, the late David Swensen was one of the foremost innovators and most successful practitioners of institutional investing. Remarkably, he also wrote one of the best books ever for individual investors. Unconventional Success shows why on average, mutual fund investors significantly underperform the funds they own: They trade excessively, buying at the highs and selling at the lows, creating tax inefficiencies in the process. Swensen also valuably details hazards to avoid in fund selection. 

Edmonton-based author Ernie Zelinski is probably best known for this self-published international bestseller.

Zelinski semi-retired at 30 after being fired from an engineering job. One of his first books was called The Joy of Not Working, and he later published The Joy of Being Retired: 365 Reasons Why Retirement Rocks—and Work Sucks!. But the one that really struck a nerve for FIRE proponents was How to Retire Happy, Wild and Free, subtitled “Retirement wisdom that you won’t get from your financial advisor”.

Zelinski sugar-coats the content with pull-out quotes and a few cartoons. As the back-cover blurb of my 2014 edition proclaims, “Retirement is the beginning of life, not the end.” It follows that Zelinski believes that the earlier you take Early Retirement, the better, and encourages readers to pluck up the courage to do just that.

To that end, his focus on frugality allows him to… show more.

There was a death in my family years back, and somehow after a long and wrenching day at the hospital, we were sitting around my dining room table at a late-night long-delayed dinner – and we were laughing. My brother came into the kitchen, worried about the children present: what were they learning? I answered: They’re learning how to bury us. Death, even death – and I am heavily grieving a loss right now – can be a moment for laughter, the sheer absurdity of life, the grief and sorrow expressed in crying and in laughing. There are other good books that do this, that take a more intellectual approach – but honestly, I admire the chutzpah of Greenberg editing a book of cartoons on death. 

The range is from the silly, the grim reaper at the door introducing the fat lady, ‘here to sing for you,' to ones that… show more.

Immigrants often try to reunite their families once they settle in their new home countries. This book looks at the experiences of elder Cantonese parents who have followed their children from China to the US. Newendorp’s sensitive ethnography reveals the joys, strains, and tensions as reunited families renegotiate the rules around family support, filial duty, and the rearing of Chinese-American grandkids. 

Bo Burlingham is an original editor for Inc. Magazine, leading that publication from its founding in Boston through its acquisition and relocation to New York CIty. This collection of “real life” exiting stories is entertaining and a quick read. The subjects are actual business owners, although most had middle-market companies that attract far more interest than the average Main Street (Under $3,000,000 value) businesses. As the author says, “No two exits are exactly alike.” 

Essential Skill #1 for Creatives: the breadwinner mindset

Creative professionals tend to be number-phobes and therefore believe they are doomed to be “starving artists.” That’s why, when I heard the title of Jennifer Barrett’s book, I knew I had to invite her to be a guest on my podcast. She writes clearly and simply about the “breadwinner” mindset. Plus, we share the belief that there is nothing more empowering than having in place the mindset, the money, and the marketing so you are free to walk away from any situation or client that isn’t a good fit. That’s the only way to bring your dream business to life.

I like authors who back up statements with research. Ken Dychtwald, CEO of Age Wave, has been studying the Boomer generation for more than three decades, and uses his research to not only demonstrate how this generation has transformed retirement, but also provides important insights for those who work with, sell to, or are Boomers themselves. Virtually every page has a nugget of useful and applicable information.

I’ve always like the phrase “Work Optional” to describe the state of being financially independent enough that you don’t have to work for money anymore, but nevertheless choose to for reasons like having a purpose, or structure.

Work Optional is also the title of another fine American book on Financial Independence, bearing the subtitle Retire Early the Non-Penny-Pinching Way. The author is an American woman, Tanja Hester, who “retired” early at age 38, along with her husband Mark, who was then 41. I put the word “retired” in quotes because, as is usually the case with advocates of the so-called FIRE movement (Financial Independence, Retire Early), Hester didn’t actually retire to do nothing.

Generally, I find that when FIRE proponents say they “retired” at 30 or 40, what they really mean is they quit working as salaried employees for a corporation, to launch what amounts to an encore career built… show more.

Since I write books about retirement, I love to read what others have written. Wes Moss’s book is fun, easy to read, helpful for retirees, and his research describes the ten most important habits for a “healthy, secure, and joyful life.”

My favorite coffee mug has this wonderful advice: “Live a Life You Don’t Need a Vacation From.” I find that Wes Moss’s book closely aligns with my own beliefs about achieving a satisfying, rewarding, and healthy retirement, and it provides a concrete framework to get there.